The biggest upsets in Kentucky Derby history

May 6th, 2023

Everyone loves a winner, especially when they pay off at astronomical odds. We've dusted off the record books and have found the five biggest Kentucky Derby upsets of all time, all of whom shocked the world with their unlikely finishes. We've also included information below on how much bettors stood to make by backing these remarkable underdogs.

5. Lil E Tee (1992)

In many ways, Lil E Tee's victory at the 1992 Kentucky Derby was far less shocking than Arazi's loss. The Francois Boutin-trained horse was tipped to be a superstar in the making and was the odds-on favorite after his biggest rival, AP Indy, was scratched earlier in the week. But Arazi emptied in the home straight and found nothing. He finished eighth, which at the time was the worst result for a Derby favourite in history.

Lil E Tee wasn’t considered to have much racing potential as a yearling, but he proved the doubters wrong when it mattered underneath the twin spires. He came with a challenge off the pace, and stunned the world by winning by half a length.

The payout for Lil E Tee’s win was $35.60

4. Giacomo (2005)

The 2005 Kentucky Derby was another story of a poor performance from a favourite – this time Bellamy Road. Bellamy Road was sent off 5-2 after winning four of his five races up to that point, including the Wood Memorial Stakes in New York. He disappointed though, and came in seventh.

The finish was a thrilling battle between two outsiders. Giacomo was 50-1, and his only win was in a maiden race before the Derby, while Closing Argument for Kiaran McLaughlin had 70-1 odds. Giacomo didn’t get away well, and after three-quarters of a mile was 18th of the 20 runners. He started making ground at the turn, but had to navigate plenty of traffic up the straight. When the gap did open, Giacomo flew through it and won by half a length.

The payout for Giacomo’s win was $102.60

3. Country House (2019)

The 145th Kentucky Derby might have been the most controversial ever. The second-favourite, Maximum Security, crossed the line first, but there was a shocking twist to come.

The jockeys of Country House and Long Range Teddy both objected to the result, and a Steward’s Decision was called. It took 22 minutes, but eventually the stewards decided that Maximum Security veered out into War of Will, who consequently impeded Long Range Toddy. He then interfered with Bodexpress, who checked sharply and hit Country House.

Maximum Security had corrected himself and gone on to win clearly from Country House, but that domino effect from his swerve would come back to haunt him. He was the first - and only - Derby "winning" horse to be disqualified for an infraction in the race, and Country House was given the roses at odds of 65-1.

The payout for Country House’s win was $132.40.

2. Mine That Bird (2009)

This running of the Kentucky Derby was so shocking they made a movie about it – when Hollywood is involved you know it must be a good story. Nobody saw Mine The Bird coming, not even NBC broadcaster Tom Durkin, who almost completely missed the winner as he was busy describing the battle between Pioneerof the Nile and Musket Man in second and third.

Mine That Bird was eight lengths off the field at the gates after a poor start, but jockey Calvin Borel used his ground-saving technique tight on the rail to bring Mine That Bird back into contention. He exploded after the final turn and shot up the rail to not only win at huge odds, but win by six-and-three-quarter lengths, the biggest winning margin in more than 60 years.

The story was made into the 2014 film 50 to 1, and Mine That Bird entered the Canadian Racing Hall of Fame a year later. The payout for his win was $103.20.

1. Donerail (1913)

The biggest shock of them all is more than 100 years old and remains an unbelievable result. Ridden by Roscoe Goose and trained by Thomas P. Hayes, Donerail remains the biggest outsider to ever win the Run for the Roses.

In the race itself, Donerail came from off the pace to swoop late and win by just half a length. At odds of 91-1, he continues to hold the title as the longest shot to win the Kentucky Derby, and that is a record unlikely to be beaten.

Incredibly, Donerail’s win paid out an astronomical $184.90.